2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 22609585, compound

HRID 2306789Notes

Reaction equation

HRID 2306789 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14])[CH:9]=[C:8](/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[CH2:7][CH2:6]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14])[CH:9]=[C:8](/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22609469HCID 22609469, compound

Product 1

HCID 22609585HCID 22609585, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Added to a solution of 100 mg (0.34 mmol) of 3-(3,4-dihydro-6,7,8-trimethoxy-2-naphthyl)prop-(2E)-enoic acid synthesized by the process described in Referential Example 6 in toluene (2 ml) was 102 mg (0.41 mmol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone, and the mixture was stirred for 1 hour and 30 minutes at 100° C. The reaction mixture was concentrated under reduced pressure, and the resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 88 mg (yield: 88%) of crude crystals of the title compound. The crude crystals were recrystallized from chloroform-hexane, thereby obtaining a pale red crystalline powder.

Workup

  1. customsynthesized by the process
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6ec28ec4f2854b40b7b1083c41d54f0e
Source dataset
uspto-grants-2004_12
Patent number
US06828316B2

Reaction notes

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